Synthesis of Methylpyridine Derivatives. XXXIV. Condensation of Acetoacetamide with Ketones to form Pyridone Derivatives

スポンサーリンク

概要

• 論文の詳細を見る

• Condensation of acetoacetamide (1) with acetone in polyphosphoric acid (PPA) gave 4,6-dimethyl-2 (1H)-pyridone (2a) in 32% yield. Similarly, the amide 1 was condensed with 2-butanone, 2-pentanone, 3-pentanone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone, and propiophenone to give the corresponding pyridone derivatives (2b-i) in 13-76% yields. Condensation of the amide 1 with acetylacetone and ethyl acetoacetate gave 3-acetyl-4,6-dimethyl-2 (1H)-pyridone (5) and ethyl 4,6-dimethyl-2 (1H)-pyridone-5-carboxylate (6), respectively. Self-condensation of the amide 1 in PPA gave 3-acetyl-4-hydroxy-6-methyl-2 (1H)-pyridone (7).

• 公益社団法人日本薬学会の論文
• 1980-07-25

著者

• 佐藤 雅之

  静岡県立大学薬学部

• 佐藤 雅之

  Pharmaceutical Institute, Tohoku University

• 加藤 鉄三

  東北大学 薬

• 加藤 鉄三

  Pharmaceutical Institute Tohoku University

• 伊藤 哲夫

  Pharmaceutical Institute Tohoku University

• 加藤 鉄三

  Pharmaceutical Institute. Tohoku University

• 野田 昌樹

  Pharmaceutical Institute, Tohoku University

• 野田 昌樹

  Pharmaceutical Institute Tohoku University

関連論文

• Diketeneより誘導された化合物, ならびに関連化合物の抗腫瘍性スクリーニング
• General Pharmacological Actions of N-Acetoacetyl-3-hydroxytyrosine
• A Novel Synthesis of β-Ketothioesters
• A Novel Synthetic Method for Tetronic Acids from 1,3-Dioxin-4-ones via Intra- or Intermolecular Ketene Trapping
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XVIII. : Synthesis of Azetidin-2-ones from 1,3-Dioxin-4-ones via 3-Hydroxycarboxamides
• Photoaddition of 2-Quinolone and 2-Pyridone Derivatives to Diketene : On the Regioselectivity of the Photoaddition
• Studies on Ketene and Its Derivatives. XCV. Reaction of Diketene with Acyl Azides
• Synthesis of dl-Dehydroiridodiol
• Studies on Ketene and Its Derivatives. CI. Reaction of Diketene with 4-Amino-methylpyridine 1-Oxides
• 1,3-Oxazine化学の最近の進歩 (ヘテロ環の化学-5-)
• Synthesis of Methylpyridine Derivatives. XXX. Reaction of Active Methylene Compounds with 6-Methyl-2-phenyl-4H-1,3-oxazin-4-one and 2-Ethoxy-2,6-dimethyl-2H-1,3-oxazin-4 (3H)-one to give 3-Acetylpyridone Derivatives
• Keteneおよびその誘導体の研究(第65報)KeteneとKetene Acetalとの反応
• Keteneおよびその誘導体の研究(第61報)第一アミンとChloroketene Diethylacetalとの反応
• Keteneおよびその誘導体の研究(第59報)5-Acetyl-2,6-dimethyl-4(3H)-pyrimidoneの閉環反応
• Studies on Ketene and Its Derivatives. LVII. Reaction of Diketene with β-Diketones
• Keteneおよびその誘導体の研究(第55報)第一アミンとKetene Acetalとの反応
• Studies on Ketene and Its Derivatives. LIV. Reaction of Diketene with Ketene Acetals
• ケテンおよびその誘導体の研究(第50報)脂肪族イミドエステルとジケテンとの反応
• Keteneおよびその誘導体の研究(第42報) : 1-Acetoacetylaziridine誘導体の環拡大反応
• Reaction of Diketene-Acetone Adduct with Enamines, Ketene Acetals, Vinyl Ethers, and β-Diketones
• Reaction of Ethyl 4-Bromoacetoacetate with Carbon Disulfide and Active Methylene Compounds
• Neighboring Group Participation of the N-Oxide Group in the Reaction of Methyl 1-Oxido-2-pyridyl Ketone Oxime with Tosyl Chloride
• Reaction of 4-Haloacetoacetate with Phenols in the Presence of Aluminum Chloride
• Studies on Ketene and Its Derivatives. CVII. Photoreaction of Diketene with 6-Methyluracil
• Studies on Ketene and Its Derivatives. CVI. Photoreaction of Diketene with N-Phenylmaleimide and Dimethyl-N-phenylmaleimide
• Studies on Ketene and Its Derivatives. CII. Reaction of Diketene with Cyanamide Derivatives
• アセトアセトアミド誘導体を用いたBiginelli反応
• ケテンおよびその誘導体の研究(第104報)3-アミノクロトンアミド誘導体とジケテンとの反応
• ジケテンのエキソメチレン二重結合の新しい付加反応
• ケテンおよびその誘導体の研究(第99報)ジケテンとイソキノリンとの反応(補遺)
• Studies on Ketene and Its Derivatives. XCVII. Photoreactions of Diketene with Maleic Anhydride and Dimethylmaleic Anhydride
• Isoquinolinium MethylidesとKetone類との反応
• Studies on Ketene and Its Derivatives. XCVI. Synthesis of Pyrido [2,1-b] benzoazoles
• Reaction of Ethyl Acetoacetate with Isoquinolinium and Pyridinium Ylides
• Synthesis of Methylpyridine Derivatives. XXXII. Reaction of Pyridine, Quinoline, and Isoquinoline with 4-Bromoacetoacetic Acid Derivatives and Synthesis of Indolizine Derivatives
• Reaction of Diazomethane with 2-Acetyl-5,5-diphenyl-2,4-pentadienoic Acid and Related Compounds
• Studies on Ketene and Its Derivatives. LXXXIV. Reaction of Diketene with Tetrazole Derivatives
• Studies on Ketene and Its Derivatives. LXXVII. Reaction of Diketene with Pyridineformimidates and Related Compounds to give 1,3-Oxazin-4-one Derivatives
• Studies on Ketene and Its Derivatives. LXXV. Reaction of Diketene with N-Benzylacetimidate and Lactim Ethers to give 1,6-Naphthyridine Derivatives
• Studies on Ketene and Its Derivatives. CXVIII. Nickel- or Palladium-Catalyzed Reaction of Diketene with Organometallics. Synthesis of 3-Substituted 3-Butenoic Acids
• STUDIES ON KETENE AND ITS DERIVATIVES. CXV. REACTION OF DIKETENE WITH ORGANOMETALLICS IN THE PRESENCE OF THE NICKEL- OR PALLADIUM-PHOSPHINE COMPLEX
• hPIV-1シアリダーゼ阻害活性をもつシアル酸誘導体の合成研究
• 研究開発情報 フルオラス・タグ法による抗シアリダーゼ活性をもつシアル酸誘導体の効率的合成研究
• P2-101 水道水中の変異原物質MXの付加体形成に関する研究(環境変異原)
• ケテン化学の新展開:α-オキソケテンの合成と反応
• Addition of Molecular Fluorine to Azlactones : General Synthetic Method of erythro-β-Fluorinated α-Amino Acids
• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines : Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst
• Facile Synthesis of 5α-Fluorocholestan-3-one from 4-Cholesten-3-one via Molecular Fluorine Addition and Reductive Defluorination
• Use of 1,3-Dioxin-4-ones and Related Compounds in Sythesis. XXXVIII. Use of 1,3-Dioxin-4-ones Having a Fluorine or Trifluoromethyl Group at the 5-Position as _π2 Components in [2+2]-Photocycloaddition and Diels-Alder Reactions
• l-MENTHYL (2S)-2-PHENYL-3-(p-ANISYL)-(5Z)-BENZYLIDENE-4,6-DIOXO-1,3-OXAZINE-2-CARBOXYLATE : A NEW CHIRAL HETERODIENE AND MICHAEL ACCEPTOR
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis XX. : (6S, 7S, 10R)- and (6R, 7S, 10R)-7-Isopropyl-10-mythyl-4-oxo-1,5-dioxaspiro[5.5]undec-2-enes; Synthesis and Their Use in Enantiomerically Pure Corey Lactone Analogue Synthesis
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XVII. : Chiral Spirocyclic 4-Oxo-1,3-dioxin-5-carboxylates : Asymmetric Synthesis of Carbocyclic C-Nucleoside Precursors
• Synthesis of Nucleosides and Their Related Compounds. XII. : Menthyl 2,4-Dioxo-1,3-oxazine-5-carboxylates : New Dienophiles for the Asymmetric Diels-Alder Reaction Directed towards Synthesis of Carbocyclic C-Nucleosides
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis.XVI. : 4-Oxo-1,3-dioxin-5-carboxylic Acids and Related Compounds : Versatile Synthetic Intermediates for the Synthesis of 6-Unsubstituted Six-Membered Heterocyclic Compunds
• キラルな1,3-ジオキシン-4-オン類の不斉有機合成への利用
• 1,3-ジオキシン-4-オン類の合成と有機合成への応用 : 最近の進歩
• A NEW METHOD FOR INTRODUCING THE 2,2-DICHLOROETHYL GROUP AT THE 3 POSITION OP THE 2-QUINOLONE SYSTEM, AND THE SYNTHESIS OF DICTAMNINE(Communication to the Editor)
• Cycloadditions in Syntheses. XXXII. Intramolecular Photocycloaddition of 4-(ω-Alkenyloxy)quinolin-2(1H)-one: Synthesis of 2-Substituted Cyclobuta[c]quinolin-3(4H)-ones(Organic,Chemical)
• Reaction of β-Aminocrotonamide with N-Acylated Amino Acid Esters to give 2-Acylaminoalkyl-6-methylpyrimidin-4 (3H)-ones and Their Ring Closure with Polyphosphoric Acid (PPA)
• Ring Transformation of 5-Oxo-4-oxaspiro [2.3] hexanes
• Studies on Ketene and Its Derivatives. XCIV. Reaction of Diketene with Diazoacetone and 2-Diazoesters
• ドクササコの有毒成分とその薬理作用
• Chemical Reactions of Bikaverin
• Studies on Ketene and Its Derivatives. LIII. Reaction of Diketene with Diazoacetophenone and Ethyl Diazoacetate
• Studies on Ketene and Its Derivatives. XLVIII. Reaction of Diketene with Hydroxylamine
• Studies on Ketene and Its Derivatives. XLVII. Reaction of 2-Aminopyridine with Diketene
• Studies on Ketene and Its Derivatives. XLVI. Mass Spectrometric Studies of 3-Acetyl-4-hydroxy-6-methyl-1-pyridyl-2-pyridones and N-Pyridyl-2,6-dimethyl-4-pyrone-3-carboxamides
• キノリン誘導体の塩素化反応
• Methylpyridine誘導体の合成(第29報)Methylpyridineおよび同族体のAryl化反応
• Studies on Ketene and Its Derivatives. LX. Reaction of Diketene with Quinoline 1-Oxide (Supplement)
• Synthesis of Methylpyridine Derivatives. XXVII. Synthesis of 1,3-Disubstituted-4-oxo-quinolizine and 2,4-Disubstituted-1-oxo-benzo [c] quinolizine Derivatives
• ケテンおよびその誘導体の研究(第58報)3-Aminocrotonamideとα, β-不飽和カルボン酸エステル類との反応
• Keteneおよびその誘導体の研究(第56報)Pyrrolidylidene誘導体とDiketeneによる5-Methyl-8-substituted-1,2,3,7-tetrahydroindolizine-7-oneの合成
• Methylpyridine誘導体の合成(第26報)3-Acylamido-4-chloro-2,6-lutidineの液体アンモニア中カリウムアミドによる閉環反応
• Studies on Ketene and Its Derivatives. XLIX. Reaction of Diketene with β-Ketoesters to give Ethyl Orsellinate, Divarate, Olivetol Carboxylate, and Sphaeropherol Carboxylate
• Keteneおよびその誘導体の研究(第45報) : 2-Alkyl-2-imidazolineとDiketeneとの反応
• 3-Amino-4-methyl-2-pentenamide, 2-Amino-1-cyclohexene-1-carboxamideおよび3-Amino-2,4-diphenyl-2-butenamideの合成ならびにそれらを用いた4(3H)-Pyrimidone誘導体の合成
• Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H, 4H-1,3-dioxin-4-ones
• Reaction of 2,2-Dimethyl-1,3-dioxin-4-ones with Imines, Carbodiimides, and Isocyanates
• Reaction of 2,2,6-Trimethyl-1,3-dioxin-4-one with Imines
• Synthesis of 1,3-Dioxin-4-one Derivatives
• Novel Annelation Method to Pyridine and Isoquinoline by Photochemical Means
• Synthesis of N-Acylacetoacetamide using 2,2,6-Trimethyl-1,3-dioxin-4-one
• Studies on Ketene and Its Derivatives. CV. Photoreaction of Diketene with sec-Alcohols
• Synthesis of Methylpyridine Derivatives. XXXIV. Condensation of Acetoacetamide with Ketones to form Pyridone Derivatives
• Studies on Ketene and Its Derivatives. XCII. Reaction of Diketene with Benzaldehyde, Cinnamaldehyde, and β-Phenylcinnamaldehyde
• Studies on Ketene and Its Derivatives. LXXXVII. Photoreaction of Diketene with 3-Acetoxy-5,5-dimethyl-2-cyclohexenone
• Studies on Ketene and Its Derivatives. LXIX. Reaction of Diketene with Hydrazobenzenes
• Studies on Ketene and Its Derivatives. LXVII. Photoreaction of Benzophenone and Benzaldehyde with Diketene
• ケテンおよびその誘導体の研究(第52報)ジケテンとα(β)-アミノニトリルとの反応
• ケテンおよびその誘導体の研究(第51報))α-アミノ酸アミドとジケテンとの反応
• Studies on Ketene and Its Derivatives. XLI. Reaction of α-Aminoketone with Diketene
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XIII. : Synthesis of 5-Halo-1,3-dioxin-4-ones and Their Conversion to 5-Alkyl Derivatives
• Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis. XI. : 2,2-Dimethyl-1,3-dioxin-4-one as a Synthetic Equivalent of Formylketene : Synthesis of Heterocyclic Compounds
• Reaction of 2,2,6-Trimethyl-1,3-dioxin-4-one with Isoquinolinium and Pyridinium Ylides
• ジケテンのエキソメチレンニ重結合の新しい付加反応
• 1, 3-ジオキシン-4-オン誘導体の合成とその有機合成への利用
• 光化学的周辺環状反応を用いる生理活性化合物の合成
• Reaction of 2,2-Dimethyl-1,3-dioxin-4-one Derivatives with Pyridinium (Isoquinolinium) Methylides and Cyano Compounds
• Studies on Ketene and Its Derivatives. XXXI. 2-Acetonyloxazolines

もっと見る 閉じる

スポンサーリンク